diff --git a/src/raycast_api/__init__.py b/src/raycast_api/__init__.py
index 3b9e026..6d81115 100644
--- a/src/raycast_api/__init__.py
+++ b/src/raycast_api/__init__.py
@@ -15,6 +15,7 @@ if TYPE_CHECKING:
         Tool,
         ToolCall,
         UserPreferences,
+        UserPreferencesArg,
     )
     from raycast_api.client import Client, RetryPolicy, SSEEvent
     from raycast_api.config import Config
@@ -38,6 +39,7 @@ __all__ = [
     "Tool",
     "ToolCall",
     "UserPreferences",
+    "UserPreferencesArg",
 ]
 
 
@@ -65,6 +67,7 @@ def __getattr__(name: str) -> Any:
         "Tool",
         "ToolCall",
         "UserPreferences",
+        "UserPreferencesArg",
     }:
         from raycast_api.ai import (
             Attachment,
@@ -78,6 +81,7 @@ def __getattr__(name: str) -> Any:
             Tool,
             ToolCall,
             UserPreferences,
+            UserPreferencesArg,
         )
 
         return {
@@ -92,5 +96,6 @@ def __getattr__(name: str) -> Any:
             "Tool": Tool,
             "ToolCall": ToolCall,
             "UserPreferences": UserPreferences,
+            "UserPreferencesArg": UserPreferencesArg,
         }[name]
     raise AttributeError(name)
diff --git a/src/raycast_api/ai/__init__.py b/src/raycast_api/ai/__init__.py
index efe9901..48ac381 100644
--- a/src/raycast_api/ai/__init__.py
+++ b/src/raycast_api/ai/__init__.py
@@ -6,7 +6,7 @@ dataclasses, and own the small amount of business logic the chat endpoint
 needs (preamble injection, source-specific defaults, SSE → typed chunks).
 """
 
-from raycast_api.ai.chat import ChatAPI, ChatResult, ChatStreamChunk
+from raycast_api.ai.chat import ChatAPI, ChatResult, ChatStreamChunk, UserPreferencesArg
 from raycast_api.ai.files import FileMetadata, FilesAPI
 from raycast_api.ai.me import MeAPI
 from raycast_api.ai.models import ModelInfo, ModelsAPI, ModelsResponse
@@ -37,4 +37,5 @@ __all__ = [
     "Tool",
     "ToolCall",
     "UserPreferences",
+    "UserPreferencesArg",
 ]
diff --git a/src/raycast_api/ai/chat.py b/src/raycast_api/ai/chat.py
index 3bfaba5..df62f10 100644
--- a/src/raycast_api/ai/chat.py
+++ b/src/raycast_api/ai/chat.py
@@ -26,8 +26,9 @@ from __future__ import annotations
 
 import json
 import uuid
+from collections.abc import Callable
 from dataclasses import dataclass, field
-from typing import TYPE_CHECKING, Any
+from typing import TYPE_CHECKING, Any, TypeAlias, Union
 
 from raycast_api.ai.types import (
     ChatStreamChunk,
@@ -40,12 +41,20 @@ from raycast_api.ai.types import (
 )
 
 if TYPE_CHECKING:
-    from collections.abc import AsyncIterator, Callable
+    from collections.abc import AsyncIterator
 
     from raycast_api.ai.models import ModelInfo
     from raycast_api.client.http import Client
 
 
+UserPreferencesArg: TypeAlias = Union[  # noqa: UP007
+    UserPreferences,
+    bool,
+    None,
+    Callable[[], "UserPreferencesArg"],
+]
+
+
 _SOURCE_DEFAULTS: dict[Source, dict[str, Any]] = {
     Source.AI_CHAT: {
         "system_instructions": "markdown",
@@ -354,7 +363,7 @@ class ChatAPI:
         message_id: str | None = None,
         system_instructions: str | None = None,
         additional_system_instructions: str | None = None,
-        user_preferences: UserPreferences | None | bool = True,
+        user_preferences: UserPreferencesArg = True,
         temperature: float | None = None,
         reasoning_effort: str | None = None,
         tools: list[Tool | RemoteTool | str] | None = None,
@@ -481,7 +490,7 @@ class ChatAPI:
         source: Source = Source.AI_CHAT,
         system_instructions: str | None = None,
         additional_system_instructions: str | None = None,
-        user_preferences: UserPreferences | None | bool = True,
+        user_preferences: UserPreferencesArg = True,
         temperature: float | None = None,
         reasoning_effort: str | None = None,
         tools: list[Tool | RemoteTool | str] | None = None,
@@ -519,13 +528,15 @@ class ChatAPI:
 
     @staticmethod
     def _coerce_preferences(
-        value: UserPreferences | None | bool,  # noqa: FBT001
+        value: UserPreferencesArg,
     ) -> UserPreferences | None:
+        if isinstance(value, UserPreferences):
+            return value
         if value is True:
             return UserPreferences.auto()
         if value is False or value is None:
             return None
-        return value
+        return ChatAPI._coerce_preferences(value())
 
     @staticmethod
     def _today_iso() -> str: